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What The Founder's Dilemmas Is About

For anyone thinking of starting something with a friend
No. 178Money & BusinessPart 11 of 11Fact-checked Oct 10, 2026
Video2:19 · English voice (AI) · English subtitles

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Three years after a startup opens its doors, half of its founders are no longer running it. By the day it goes public, fewer than a quarter are still at the helm. Where did they go? A Harvard Business School professor spent about ten years studying nearly ten thousand founders, and wrote a book: The Founder's Dilemmas. He found that much of the trouble doesn't start later. It starts with a few early choices that feel completely natural. Let's follow two friends from opening day.

First fork in the road: who do you build it with? The easy pick is friends and family. You know each other, you click right away. But the book says this road hides the deepest holes. Friends can't say the hard things out loud. If it falls apart, you lose the business and the friendship. Second fork: how do you split the company? In the book's data, more than seven in ten teams settle the split in the first month. A third simply go fifty-fifty.

Fifty-fifty sounds fairest. But on that day, nobody knows who will work harder, or who will walk away halfway. What's fair today can be the least fair thing three years on. One fix from the book: don't lock it all in at once. Agree that each share is earned bit by bit over time. If someone leaves early, the unearned part stays with the company. The third fork holds the answer to that opening number: do you want to be rich, or do you want to be king?

To grow big, you bring in investors and more experienced managers. As the money comes in, the top job and the final say slowly slip away. Most founders who stepped down were asked to leave by their investors. Later the author looked at over six thousand American startups: for each thing a founder kept a grip on, the top job, or the board, the company was worth about a fifth less on average. So there's no single right answer. Let go, and your shares are worth more. Hold on, and the company stays smaller, but it's yours to run. The book asks just one thing: before you open, decide which one you want.

To be fair: most of this data comes from American tech startups. Not all of it fits a small restaurant. Teaming up with friends, splitting it fifty-fifty, staying the boss: the three choices that seemed easiest are the ones to think through first. What did you used to think was the fair way to split a partnership?

1

Three years in,
half the founders are out

1/2no longer in charge after three years
<1/4still at the helm when the company goes public

That's what Harvard Business School professor Noam Wasserman found in 212 American startups. He spent about ten years studying nearly ten thousand founders and wrote this book.

Not to be confused with Christensen's The Innovator's Dilemma, which is about big companies losing to small ones. This one is about the founders' own early choices.

Most trouble isn't born later. It's born in three choices that feel natural at the start.

2

Fork one:
teaming up with friends

WHAT WE THINK
We know each other. We click.
Friends and family are the easy pick at the start.
THE BOOK SAYS
This road has the deepest holes
Hard things go unsaid. If it falls apart, you lose the business and the friendship.

The book doesn't say "never partner with friends." It says: the closer you are, the more you need to say the hard things up front.

3

Fork two:
fifty-fifty

73%settle the split in month one
1/3just go fifty-fifty

Fifty-fifty sounds fairest. But on that day, nobody knows who will work harder, or who will walk away halfway.

Fair today can be the least fair thing in three years.

1. Agree firstShares are earned bit by bit over time.
2. Earn itWhoever puts in more, gets more.
3. Leave earlyWhat you haven't earned stays with the company.
4

Fork three:
rich or king?

To grow big, you bring in investors and more experienced managers. As money comes in, the top job and the final say slowly slip away. Most founders who stepped down were asked to leave by investors.

Let goBigger company, more valuable shares
Hold onSmaller company, but you call the shots

Later the author looked at 6,130 American startups: for each thing a founder kept a grip on (the top job, or the board), the company was worth about a fifth less on average.

No single right answer. Decide which one you want before you open.

5

Where the book
doesn't reach

Most of the data is from American tech startups Not all of it fits a small restaurant. And companies whose founders keep control may simply need less outside money: the two go together, but one doesn't fully cause the other.
Friends, fifty-fifty, staying the boss
The three choices that seemed easiest are the ones to think through first. What did you used to think was the fair way to split a partnership?
Created by Samshang × Maddox
Sources: Noam Wasserman, The Founder's Dilemmas, Princeton University Press 2012 (Chinese edition: Huazhong University of Science and Technology Press 2017, Douban listing); Wasserman, "The Founder's Dilemma", Harvard Business Review, February 2008; HBS Working Knowledge, "How to Sink a Startup"; Wasserman, "The Throne vs. the Kingdom: Founder Control and Value Creation in Startups", Strategic Management Journal 2017.
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